WO2014195210A1 - Sulfated oligohydroxycarboxylic acid esters, and use thereof - Google Patents

Abstract

The present invention relates to sulfated oligohydroxycarboxylic acid esters, to cosmetic and pharmaceutical agents containing said esters, and to the use of said esters as anionic surfactants.

Description

 Sulfated esters of oligohydroxycarboxylic acids and their use

BACKGROUND OF THE INVENTION The present invention relates to sulfated esters of oligohydroxycarboxylic acids, to cosmetic and pharmaceutical compositions containing these esters, and to the use of these esters as anionic surfactants.

STATE OF THE ART

Anionic surfactants are among the most widely used surface-active compounds and are widely used not only in detergents and cleaners but also in the field of cosmetics. Conventional anionic surfactants, such as those used primarily in cosmetics, are the salts of alkyl ether sulfates (alkylpolyether sulfates, fatty alcohol polyglycol ether sulfates, and also ether sulfates). They are characterized by strong foaming power, high cleaning power, low hardness and fat sensitivity and are widely used for the production of cosmetic products such as hair shampoos, foam or shower baths, but also in hand dishwashing detergents.

For many current applications, anionic surfactants are subject to further requirements in addition to good surface-active action. Especially in cosmetics, a high dermatological compatibility is required. Furthermore, a sufficient solubility in water, good compatibility with as many of the active ingredients and auxiliaries used in cosmetics, good foaming power and good rheology behavior are generally desirable. Furthermore, there is a need for anionic surfactants which can be prepared at least in part from biogenic sources and especially renewable raw materials. Furthermore, there is also a need for surfactants which have no alkoxylated groups and thus make the use of ethylene oxide in particular unnecessary for their preparation.

EP 0 530 866 A1 describes sulfated esters of alkanecarboxylic acids and their use as surface-active compounds which are hydrolyzed on contact with the skin and release an active component (eg a hydroxycarboxylic acid ester).

DE 40 03 096 A1 describes sulfated hydroxycarboxylic acid esters and their use as surface-active substances. The example A for the preparation of lactic acid lauryl ester described on page 4 of this document is not executable Technical teaching for the preparation of lauryl esters of lactic acid oligomers. Thus, it is already not possible to heat the esterification using toluene as entraining agent, which forms an azeotrope with a boiling point of about 80 to 90 ° C with the liberated in the reaction water, using a water to the specified 225 ° C.

DE 43 40 042 A1 describes the use of sulfate surfactants, as described in DE 40 03 096 A1, as surface-active substances in cleaning and rinsing agents for cleaning and rinsing hard surfaces.

It is an object of the present invention to provide novel compounds which are advantageously suitable as surface-active compounds for various applications. They should be especially suitable to cover a complex range of requirements, as described above. In particular, it should be possible to provide surfactant-containing formulations which have performance properties which are at least comparable to anionic surfactants known from the prior art based on petrochemical components and / or based on alkylene oxides.

Surprisingly, it has now been found that this object is achieved by sulfated esters of oligohydroxycarboxylic acids.

SUMMARY OF THE INVENTION The first object of the invention is compounds of the general formula (I)

worin

wherein

R ^{1 is} hydrogen or a linear or branched aliphatic hydrocarbon radical having 1 to 30 carbon atoms and 0, 1, 2 or 3 double bonds, the radicals R ^{2 are} independently selected from hydrogen, methyl,

Ethyl, -OA, -COOR ⁴ , -CH ₂ -OA and -CH ₂ -COOR ⁴ , wherein the radicals R ^{4 are} hydrogen or a linear or branched aliphatic hydrocarbon radical having 1 to 30 carbon atoms and 0, 1, 2 or 3 double bonds , the radicals R ^{3 are} independently selected from hydrogen, methyl,

Ethyl, -OA, -COOR ⁵ , -CH ₂ -OA and -CH ₂ -COOR ⁵ , wherein the radicals R ^{5 are} hydrogen or a linear or branched aliphatic hydrocarbon radical having 1 to 30 carbon atoms and 0, 1, 2 or 3 double bonds .

A is H or -SO3B, wherein B is hydrogen or a cation equivalent, n is an average of at least 0.1, m1 and m2 are independently 0 or 1, provided that at least one of the radicals A is -SO3B, and provided that at least one of R ¹ , R ⁴ or R ^{5 is} a linear or branched aliphatic hydrocarbon radical having 1 to 30 carbon atoms and 0, 1, 2 or 3 double bonds.

A preferred embodiment is sulfated esters of oligolactates. Thereafter, the compounds of general formula (I) are selected from compounds of formula (1.1) o o

R ¹ O- ^■ C CH (CH ₃ ) O- - C CH (CH ₃ ) OSO3B

(1.1)

wherein

R ^{1 is} hydrogen or a linear or branched hydrocarbon radical having 6 to 30 carbon atoms and 0, 1, 2 or 3 double bonds, B is hydrogen or a cation equivalent, and n stands on average for a value of at least 0.1.

Another object of the invention is a process for the preparation of compounds of general formula (I). The invention also provides the compounds of general formula (I) obtainable by this process.

Another object of the invention is a cosmetic or pharmaceutical composition containing at least one compound of general formula (I) as defined above and hereinafter.

Another object of the invention is the use of compounds of general formula (I), as defined above and hereinafter, as surface-active substances, especially as anionic surfactant for detergents and cleaners, cosmetic products, pharmaceutical agents.

DESCRIPTION OF THE INVENTION

The compounds of general formula (I) may be in the form of mixtures or as pure compounds. For the uses according to the invention are generally suitable mixtures of compounds of general formula (I), as described, for. B. are obtainable by the manufacturing method described below. The individual components of these mixtures may differ, for example, with regard to the degree of oligomerization n. If hydroxycarboxylic acids which have more than one carboxyl group and / or more than one alcoholic OH group are used for the preparation of the compounds of the general formula (I), the individual components of these mixtures may also be structural isomers from the esterification reaction their production act. Of course, it is also possible to obtain the reaction mixtures obtainable by the process according to the invention by customary separation processes, for. B. by distillation or by chromatography, to separate.

The average degree of oligomerization results for the compounds of the general formula (I) and the general formula (1.1) according to the invention by addition of 1 to the value of the variable n. In the context of the invention, cation equivalent denotes a monovalent cation or the monovalent charge fraction of a multivalent cation.

When B is a cation equivalent, it is preferably selected from alkali metal cations, NH ₄ ⁺ and cations of the formula HNE ¹ E ² E ³⁺ , where E ¹ , E ² and E ³ are independently selected from hydrogen, linear and branched Ci-C6-alkyl and linear and branched Ci-C4-hydroxyalkyl, with the proviso that one of the radicals E ¹ , E ² and E ^{3 is} different from hydrogen. Preferably, the cation equivalent is selected from Na ^+, K ^+, NH ₄ ^+, Mg ²⁺ / 2, HN (CH _{3) 3} ^+, HN (C ₂ H _{5) 3} ^+, HN (C ₂ H ₄ OH) ₃ ⁺ , H ₂ N (C ₂ H ₄ OH) ₂ ⁺ , etc.

Suitable linear or branched aliphatic hydrocarbon radicals having 1 to 30 carbon atoms and 0, 1, 2 or 3 double bonds are the corresponding

C ₁ -C 30 -alkyl radicals, C ₁ -C 30 -alkenyl radicals, C ₁ -C 30 -alkadienyl radicals and C ₁ -C 30 -alkatrienyl radicals.

At least one of the radicals R ¹ , R ⁴ or R ⁵ is preferably a linear or branched aliphatic hydrocarbon radical having 1 to 30 carbon atoms and 0, 1, 2 or 3 double bonds. In particular, R ¹ , R ⁴ and R ^{5 are} independently selected from methyl, ethyl, propyl, isopropyl, n-butyl, 2-butyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 2-methylbutyl , 3-methylbutyl, 1, 2-dimethylpropyl, 1, 1-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 2-hexyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 2 Dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1 Ethyl butyl, 2 ethyl butyl, 1-ethyl-2-methylpropyl, n-heptyl,

2-heptyl, 3-heptyl, 2-ethylpentyl, 1-propylbutyl, n-octyl, 2-ethylhexyl, 2-propylheptyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n- Tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, arachinyl, behenyl, lignocerinyl, melissinyl, isotridecyl, isostearyl, oleyl, linoleyl, linolenyl, etc.

In a preferred embodiment, at least one of the radicals R ¹ , R ⁴ or R ^{5 is} a linear or branched aliphatic hydrocarbon radical having 6 to 30 carbon atoms and 0, 1, 2 or 3 double bonds. Particularly preferably, R ¹ , R ⁴ and R ^{5 are} independently selected from n-hexyl, 2-ethylhexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl , n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, arachinyl, behenyl, lignocerinyl, melissinyl, isotridecyl, isostearyl, oleyl, linoleyl, linolenyl, and combinations thereof. The radicals R ¹ , R ⁴ and R ⁵ can be derived from pure alcohols or from alcohol mixtures. Preferably, it is industrially available alcohols or alcohol mixtures. In a preferred embodiment, R ¹ , R ⁴ and R ^{5 are} then independently selected from predominantly linear alkyl, alkenyl, alkadiene nyl- and alkatrienyl radicals, as they occur in natural or synthetic fatty acids and the corresponding fatty alcohols.

In a further preferred embodiment, R ¹ , R ⁴ and R ^{5 are} independently derived from fatty alcohols based on technical alcohol mixtures. These include z. As obtained in the hydrogenation of technical methyl esters based on fats and oils alcohol mixtures. These furthermore include the alcohol mixtures (oxo alcohols) obtained in the hydrogenation of aldehydes from the oxo process or the alcohol mixtures obtained in the dimerization of unsaturated fatty alcohols.

At least one of the radicals R ¹ , R ⁴ and R ^{5 is} preferably derived from linear saturated alcohols having 8 to 18 carbon atoms. Particularly preferably, at least one of the radicals R ¹ , R ⁴ and R ^{5 is derived} from a mixture of linear saturated C 12- / C 14 -alcohols.

Furthermore, at least one of the radicals R ¹ , R ⁴ and R ^{5 is} preferably derived from a C 16- / C 18 -fatty alcohol mixture. Mixtures of cetyl (hexadecyl) and stearyl (octadecyl) are also referred to as cetearyl.

In the compounds (I), the variables m1 and m2 preferably have the same meaning. The compounds of the general formula (I) are esters of olighydroxycarboxylic acids. These can be derived from conventional hydroxycarboxylic acids, such as lactic acid, glycolic acid, malic acid, tartaric acid, tartronic acid and mixtures thereof. Preferably, the compounds (I) are derived from lactic acid, glycolic acid, malic acid, tartaric acid or mixtures thereof. Particular preference is given to the compounds (I) derived from lactic acid.

In the compounds of general formula (I), n is preferably from 0.1 to 100, particularly preferably from 0.15 to 50, in particular from 0.2 to 20. In the compounds of general formula (1.1) n is n preferably for a value of 0.1 to 100, particularly preferably from 0.15 to 50, in particular from 0.2 to 20.

Another object of the invention is a process for the preparation of compounds of general formula (I), wherein a) at least one hydroxycarboxylic acid of the general formula (IA)

O

HOC (CHR ² ) _m ¹ CHR ³ - OH (LA) wherein R ² , R ³ and m1 are as defined in any one of claims 1 to 8, in an esterification reaction, wherein the esterification is carried out in the presence of at least one alcohol R ¹ -OH in which R ^{1 is defined} as in one of claims 1 to 8 or the product of the esterification of the hydroxycarboxylic acid (s) (IA) is subsequently reacted with at least one alcohol R ¹ -OH, b) the reaction product from step a) reacting a sulphating agent, and c) optionally at least partially neutralizing the reaction product from step b) with a base.

With respect to suitable and preferred definitions of R ¹ , R ² , R ³ , R ⁴ , R ^5, and m ¹ , reference is made in full to the foregoing for these radicals and variables.

Step a)

The esterification reaction in step a) can be carried out in several stages, wherein at least one hydroxycarboxylic acid (IA) is subjected to esterification with oligomerization and then the resulting reaction mixture, optionally after separation and / or purification, in a further esterification with at least one alcohol R ¹ -OH is implemented. Preferably, the esterification reaction for the preparation of compounds of general formula (I) in the sense of a one-pot reaction in which at least one hydroxycarboxylic acid of the general formula (IA) in the presence of at least one alcohol R ¹ -OH is subjected to esterification. The esterification reaction can be carried out by generally known methods, wherein the removal of the reaction water formed z. B. by dehydrating agents, extractive or can be carried out by distillation. Preferably, the water of reaction formed is removed by distillation. In a specific embodiment, the reaction water formed can be removed azeotropically. The reaction takes place in the presence of a solvent which forms an azeotropic mixture with water. Suitable solvents and entrainers are aliphatic and aromatic hydrocarbons, eg. As alkanes, such as n-hexane and n-heptane, cycloalkanes, such as cyclohexane and methylcyclohexane, aromatics, such as benzene, toluene and xylene isomers and so-called specialty spirits, which have boiling points between 70 and 140 ° C. Particularly preferred entrainers are cyclohexane, methylcyclohexane and toluene. Suitable apparatuses for azeotropic distillation with separation of the water of reaction and recycling of the solvent into the reaction vessel are known to the person skilled in the art. The solvent used can after esterification by conventional methods, such as. B. by distillation, optionally under reduced pressure, are removed from the reaction mixture.

Is used to esterify an alcohol R ¹ -OH with a sufficiently high boiling point, for. As a saturated or mono- or polyunsaturated fatty alcohol having at least 6 carbon atoms, it can be dispensed with in the removal by distillation of the reaction water on the use of an entraining agent.

The esterification temperature is generally in a range from about 50 to 250 ° C, more preferably from 70 to 200 ° C.

The esterification is preferably carried out at atmospheric pressure or reduced pressure. For distillative removal of the water of reaction, it is advantageous to carry out the esterification at reduced pressure. In the esterification, the pressure is preferably in a range from 1 mbar to 1, 1 bar, in particular 5 mbar to 1 bar, especially 10 mbar to 900 mbar. This applies both to the above-described single-stage and the two-stage variant of the esterification reaction.

The esterification can be carried out autocatalytically or in the presence of a catalyst. Suitable catalysts are strong acids, such as. As sulfuric acid, anhydrous hydrogen chloride, sulfonic acids, eg. For example, toluenesulfonic acid and methanesulfonic acid, and acidic ion exchangers. In the process according to the invention, preference is given to using sulfuric acid and p-toluenesulfonic acid as catalyst. The amount of the esterification catalyst is generally in a range of about 0.1 to 5 wt .-%, based on the total amount of components to be esterified. The esterification reaction preferably takes place without addition of an external solvent. This applies both to the above-described single-stage and the two-stage variant of the esterification reaction. However, it is alternatively possible to carry out the reaction according to the invention in the presence of an organic solvent which is inert under the reaction conditions or of a solvent mixture. Preference is given to aprotic solvents. The solvents used preferably have a boiling point of at least 120.degree. C., in particular of at least 140.degree. These include z. As alkylene glycol dialkyl ethers such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, etc. Also suitable for. B. Cyclohexanone (bp.: 155 ° C), N-methylpyrrolidone (bp.: 204 ° C), sulfolane (bp.: 285 ° C), nitrobenzene (bp.: 210 ° C), xylene (b.p. : 140 ° C).

The setting of the desired average degree of oligomerization (p = 1 + n) is possible in the usual way.

Thus, in the two-stage variant of the esterification reaction described above, firstly an oligomeric hydroxycarboxylic acid having the desired average degree of oligomerization (p = 1 + n) can be prepared. For this purpose, the reaction mixture is kept under dehydrating conditions for a period of time at the reaction temperature which is sufficient to achieve the desired average degree of oligomerization. Preferably, the reaction time is about 0.5 to about 24 hours, more preferably about 1 to about 20 hours. Subsequently, the oligomeric hydroxycarboxylic acid thus obtained is reacted with at least one alcohol R ¹ -OH to form the end product. The molar ratio of alcohol component R ¹ -OH to oligomeric hydroxycarboxylic acid is about 1: 1 in this variant.

In the above-described one-stage variant of the esterification reaction, at least one hydroxycarboxylic acid of the general formula (IA) is esterified in the presence of at least one alcohol R ¹ -OH. According to this variant, the setting of the desired average degree of oligomerization n is possible, for example, via the molar ratio of alcohol component R ¹ -OH to hydroxycarboxylic acid (IA). In the case of this variant, this is preferably 1: 1, 01 to 1: 200, more preferably 1: 1, 1 to 1: 100, in particular 1: 1, 15 to 1:50, especially 1: 1, 2 to 1: 20. Also according to this variant, the reaction mixture is left under dehydrating conditions for a period of time at the reaction temperature which is sufficient to achieve compounds of general formula (I) having the desired average degree of oligomerization. Preferably, the reaction time is about 0.5 to about 24 hours, more preferably about 1 to about 20 hours. Step b)

Sulfation reactions of surfactant alcohols are known in the art and z. For example, in WO 93/24453, DE 40 03 096 A1 and in "Ullmann's Encyclopedia of Industrial Chemistry", 5th Edition Bd. A25 (1994), pages 779-783 and in the references cited therein.

In principle, for sulfation of the reaction product from step a) sulfur trioxide, sulfur trioxide complexes, solutions of sulfur trioxide in sulfuric acid ("oleum"), concentrated sulfuric acid, chlorosulfonic acid, sulfuryl chloride or amidosulfonic acid can be used.

Preferably, the sulfating agent used in step b) comprises SO3 or consists of SO3. Preferably, gaseous sulfur trioxide is used in admixture with a gas which is inert under the reaction conditions of the sulfation. Preferred inert gases are nitrogen or air. In this case, the sulfur trioxide is diluted with air or nitrogen and preferably used in the form of a gas mixture with about 1 to 10, in particular 3 to 6 vol .-%, sulfur trioxide. The sulfonation with SO3 can be carried out continuously or discontinuously, but in particular in reactors which operate on the falling film principle.

Preferably, the reaction is carried out in the absence of solvents. However, it is also possible for the sulfation of olefins, aromatics, alcohols and the like usual solvents such. As orthoformic acid esters, dimethylformamide, 1, 2 dichloroethane or tetrahydrofuran, are used.

The sulfation with SO3 is preferably carried out with a molar ratio of hydroxy carboxylic acid ester to SO3 of 1: 0.9 to 1: 2.4. Particularly preferred is a range of 1: 1, 0 to 1: 1, 3.

The sulfation with SO3 is carried out, for example, at temperatures of 10 to 98 ° C. On the one hand to ensure a sufficiently low viscosity of the starting materials and on the other hand to avoid excessive thermal stress during the reaction, it is advisable to carry out the sulfonation at a temperature in the range of 20 to 90 ° C.

If chlorosulfonic acid is used as the sulfating reagent, the corresponding alcohol component is preferably used in a stirred apparatus under inert conditions. presented conditions and fed the chlorosulfonic acid. The molar ratio between alcohol component and chlorosulfonic acid is preferably 0.5: 1 to 1: 0.5, more preferably the ratio is 0.75: 1 to 1: 0.75. Most preferably, the molar ratio of alcohol component to chlorosulfonic acid is about 1: 1.

If sulfuric acid is used for esterification, it is expedient to use a 75 to 100% strength by weight, preferably 85 to 98% strength by weight acid (so-called "concentrated sulfuric acid" or "sulfuric acid monohydrate"). The esterification can be carried out in a solvent or diluent, if it is necessary for the control of the reaction, for. B. the heat is desired. As a rule, the alcoholic reactant is initially charged and the sulfating agent gradually added with constant mixing. If complete esterification of the alcohol component is desired, the sulfating agent and the alcohol component are preferably used in a molar ratio of from 1: 1 to 1: 1.5, more preferably from 1: 1 to 1: 1. 2. The esterification is preferably carried out at temperatures of from 20 to 90 ° C, more preferably 45 to 75 ° C performed. If appropriate, it may be expedient to carry out the esterification in a low-boiling, water-immiscible solvent and diluent at its boiling point, wherein the water formed in the esterification is distilled off azeotropically.

Step c)

As the base for neutralization, alkali metal bases such as caustic soda, potassium hydroxide, soda, sodium bicarbonate, potassium carbonate or potassium hydrogencarbonate, and alkaline earth metal bases such as calcium hydroxide, calcium oxide, magnesium hydroxide or magnesium carbonate and amines can be used. Suitable amines are, for. C 1 -C 6 -alkylamines, preferably n-propylamine and n-butylamine, dialkylamines, preferably diethylpropylamine and dipropylmethylamine, trialkylamines, preferably triethylamine and triisopropylamine. Preference is given to amino alcohols, for. Example, trialkanolamines, such as triethanolamine, Alkyldialkanolamine, such as methyl or ethyldiethanolamine and Dialkylalka- nolamine, such as dimethylethanolamine and 2-amino-2-methyl-1-propanol. The neutralization of the acid groups can also be carried out with the aid of mixtures of several bases. The base is particularly preferably selected from NaOH, KOH, 2-amino-2-methyl-1-propanol, triethylamine, diethylaminopropylamine, diethanolamine,

Triethanolamine, triisopropanolamine and mixtures thereof. Neutralization can be partial or complete depending on the application. For a partial neutralization z. B. 50 to less than 100% of the acid groups are neutralized. Preference is given to complete neutralization. The compounds of general formula (I) and general formula (1.1) are advantageously suitable for use as anionic surfactants. In general, they may be, for example, cosmetic compositions, pharmaceutical compositions, hygiene products, detergents and cleaners, paints, compositions for the paper industry, compositions for the textile industry, etc.

The surfactants of the invention can be used as the sole surface-active substance. Advantageously, the compounds of general formula (I) and general formula (1.1) are distinguished by their good compatibility with other surfactants.

Surfactant-containing compositions

The compounds of the general formula (I) or the general formula (1.1) according to the invention are particularly advantageously suitable for the formulation of surfactant-containing compositions. In particular, these are aqueous surfactant-containing compositions. The compounds (I) and (1.1) are distinguished in such compositions by their good water solubility, good compatibility with many of the active ingredients and auxiliaries used in cosmetics, good foaming power and good rheology behavior.

The surfactant-containing compositions according to the invention preferably have a total surfactant content of from 0.1 to 75% by weight, more preferably from 0.5 to 60% by weight, in particular from 1 to 50% by weight, based on the total weight of the surfactant-containing composition, on.

Suitable surfactants are anionic surfactants other than the compounds (I), nonionic surfactants, cationic surfactants, amphoteric surfactants and mixtures thereof.

Typical examples of anionic surfactants are soaps, alkyl sulfonates, alkylbenzenesulfonates, olefinsulfonates, alkyl ether sulfonates, glycerol ether sulfonates, methyl ester sulfonates, sulfo fatty acids, alkyl sulfates, fatty alcohol ether sulfates, glycerol ether sulfates, fatty acid ether sulfates, hydroxy mixed ether sulfates, monoglyceride (ether) sulfates, fatty acid amide (ether). sulfates, mono- and dialkyl sulfosuccinates, mono- and dialkyl sulfosuccinamates, sulfotriglycerides, amide soaps, ether carboxylic acids and their salts, fatty acid ethionates, fatty acid sarcosinates, fatty acid taurides, N-acylamino acids, such as for example, acylglutamates and acylaspartates, as well as acyl lactylates, acyl tartrates, alkyloligoglucoside sulfates, alkyl glucose carboxylates, protein fatty acid condensates and alkyl (ether) phosphates. Suitable soaps are z. As alkali, alkaline earth and ammonium salts of fatty acids, such as potassium stearate.

Suitable olefin sulfonates are z. B. by addition of SO3 to olefins of the formula R ³ -CH = CH-R ⁴ and subsequent hydrolysis and neutralization, wherein R ³ and R ^{4 are} independently H or alkyl radicals having 1 to 20 carbon atoms, with the proviso that R ³ and R ⁴ together have at least 6 and preferably 8 to 20, especially 10 to 16, carbon atoms. For the preparation and use, see the review article "J. Am. Oil. Chem. Soc.", 55, 70 (1978). The olefin sulfonates may be present as alkali, alkaline earth, ammonium, alkylammonium, alkanolammonium or glucammonium salts. Preferably, the olefin sulfonates are present as sodium salts. The hydrolyzed alpha-olefin sulfonation product, ie the alpha-olefin sulfonates, is composed of about 60% by weight of alkanesulfonates and about 40% by weight of hydroxyalkanesulfonates; Of these, about 80 to 85 wt .-% mono- and 15 to 20 wt .-% disulfonates.

Preferred methyl ester sulfonates (MES) are obtained by sulfonation of the fatty acid methyl esters of vegetable or animal fats or oils. Preferred are methyl ester sulfonates of vegetable fats and oils, eg. B. from rapeseed oil, sunflower oil, soybean oil, palm oil, coconut oil, etc.

Preferred alkyl sulfates are sulfates of fatty alcohols of the general formula R ⁶ -O-SO 3 Y, wherein R ^{6 is} a linear or branched, saturated or unsaturated hydrocarbon radical having 6 to 22 carbon atoms and Y is an alkali metal, the monovalent charge equivalent of an alkaline earth metal, ammonium, mono , Di-, tri- or tetraalkylammonium, alkanolammonium or glucammonium. Suitable fatty alcohol sulfates will preferably be obtained by sulfation of native fatty alcohols or synthetic oxoalcohols and subsequent neutralization. Typical examples of fatty alcohol sulfates are the sulfation products of caproic alcohol, capryl alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol,

Isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolyl alcohol, linolenyl alcohol, behenyl alcohol and elaeostearyl alcohol, and the salts and mixtures thereof. Preferred salts of the fatty alcohol sulfates are the sodium and potassium salts, especially the sodium salts. Preferred mixtures of fatty alcohol sulphates te are based on technical alcohol mixtures, the z. B. incurred in the high-pressure hydrogenation of technical methyl esters based on fats and oils or in the hydrogenation of aldehydes from the oxo process or in the dimerization of unsaturated fatty alcohols. For the preparation of alkyl sulfates, fatty alcohols and fatty alcohol mixtures having 12 to 18 carbon atoms and in particular 12 to 14 carbon atoms are preferably used. Typical examples include technical alcohol sulfates based on vegetable raw materials.

Preferred sarcosinates are sodium lauroyl sarcosinate or sodium stearoyl sarcosinate.

Preferred protein fatty acid condensates are wheat based vegetable products.

Preferred alkyl phosphates are mono- and Diphosphorsäurealkylester. Suitable acylglutamates are compounds of the formula (I)

(i) wherein COR ^{7 is} a linear or branched acyl radical having 6 to 22 carbon atoms and 0, 1, 2 or 3 double bonds and X is hydrogen, an alkali metal, the monovalent charge equivalent of an alkaline earth metal, ammonium, alkylammonium, alkanolammonium or glucammonium. The preparation of acylglutamates is carried out, for example, by Schotten-Baumann acylation of glutamic acid with fatty acids, fatty acid esters or fatty acid halides. Acylglutamates are commercially available from, for example, BASF SE, Clariant AG, Frankfurt / DE or Ajinomoto Co. Inc., Tokyo / JP. An overview of the preparation and properties of acylglutamates can be found in M. Takehara et al. in J. Am. Oil Chem. Soc. 49 (1972) 143. Typical acylglutamates suitable as component b) are preferably derived from fatty acids having 6 to 22 and particularly preferably 12 to 18 carbon atoms. In particular, the mono- or dialkali metal salts of acylglutamate are used. These include z. B. (trade names from Ajinomoto, USA in parentheses): sodium cocoylglutamate (Amisoft CS-1 1), disodium cocoylglutamate (Amisoft ECS-22SB), triethanolammonium cocoylglutamate (Amisoft CT-12), triethanolammonium lauroylglutamate (Amisoft LT-12) , Sodium myristoylglutamate (Amisoft MS-1 1), sodium stearoylglutamate (Amisoft HS-1 1 P), and mixtures thereof. Nonionic surfactants include, for example:

Fatty alcohol polyoxyalkylene esters, for example lauryl alcohol polyoxyethylene acetate,

 Alkylpolyoxyalkylenether, which are derived from low molecular weight Ci-C6 alcohols or C7-C3o-fatty alcohols. In this case, the ether component can be derived from ethylene oxide units, propylene oxide units, 1,2-butylene oxide units, 1,4-butylene oxide units and random copolymers and block copolymers thereof. These include, in particular, fatty alcohol alkoxylates and oxo alcohol alkoxylates, in particular of the type

RO- (R ⁸ 0) r (R ⁹ O) _s R ¹⁰ with R ⁸ and R ⁹ independently of one another = C ₂ H ₄ , C ₃ H ₆ , C ₄ H ₈ and R ¹⁰ = H, or Ci-Ci ₂ alkyl, R = C ₃ -C ₃₀ alkyl or C ₆ -C ₃ -alkenyl, r and s are independently 0 to 50, where not both be 0, as iso- tridecyl alcohol and Oleylalkoholpolyoxyethylenether,

 Alkylaryl alcohol polyoxyethylene ethers, e.g. Octylphenol polyoxyethylene ethers, alkoxylated animal and / or vegetable fats and / or oils, for example corn oil ethoxylates, castor oil ethoxylates, tallow fatty ethoxylates,

 Glycerol esters, such as glycerol monostearate,

 Alkylphenol alkoxylates, such as, for example, ethoxylated isooctyl, octyl or nonylphenol, tributylphenol polyoxyethylene ethers,

 Fatty amine alkoxylates, fatty acid amide and fatty acid diethanolamide alkoxylates, in particular their ethoxylates,

 Sugar surfactants, sorbitol esters, such as, for example, sorbitan fatty acid esters (sorbitan monooleate, sorbitan tristearate), polyoxyethylene sorbitan fatty acid esters, alkyl polyglycosides, N-alkylgluconamides,

 alkyl methyl,

 Alkyldimethylphosphine oxides, such as, for example, tetradecyldimethylphosphine oxide. Suitable amphoteric surfactants are, for. Alkylbetaines, alkylamidopropylbetaines, alkylsulfobetaines, alkylglycinates, alkylcarboxyglycinates, alkylamphoacetates or

Propionates, alkyl amphodiacetates or dipropionates. For example, cocomethylsulfopropylbetaine, laurylbetaine, cocamidopropylbetaine, sodium cocamphopropionate or tetradecyldimethylamine oxide can be used.

The cationic surfactants include, for example, quaternized ammonium compounds, in particular alkyltrimethylammonium and dialkyldimethylammonium halides and alkylsulfates, and pyridine and imidazoline derivatives, in particular alkylpyridinium halides. For example, behenyl or cetyltrimethylammonium be used. Also suitable are so-called esterquats based on quaternary triethanol-methyl-ammonium or quaternary diethanol-dimethyl-ammonium compounds with long hydrocarbon chains in the form of fatty acid esters. These include, for example, bis (acyloxyethyl) hydroxyethylammonium methosulfate. Also suitable is Dehyquart L 80 (INCI: dicocoylethyl hydroxyethyl methosulfate (and) propylene glycol).

Cosmetic and Pharmaceutical Agents The compounds of the general formula (I) and the general formula (1.1) are preferably suitable for the formulation of cosmetic and pharmaceutical products, especially of aqueous cosmetic and pharmaceutical products.

The invention further provides a cosmetic or pharmaceutical composition comprising a) at least one compound of the general formula (I) as defined above, b) at least one cosmetic or pharmaceutical active ingredient, and c) optionally at least one of the components a) and b) various cosmetic or pharmaceutical excipient.

Preferably, at least one compound of the general formula (1.1) is used as component a).

Preferably, component c) comprises at least one cosmetic or pharmaceutical carrier. Preferably, the carrier component c) is selected from i) water,

ii) water-miscible organic solvents, preferably C 2 -C 4 alkanols, in particular ethanol,

iii) oils, fats, waxes,

iv) of (iii) various esters of C6-C3o-monocarboxylic acids with monohydric, dihydric or trihydric alcohols,

v) saturated acyclic and cyclic hydrocarbons,

vi) fatty acids,

vii) fatty alcohols, viii) propellants, and mixtures thereof. Especially suitable cosmetically acceptable oil or fat components c) are described in Karl-Heinz Schräder, Fundamentals and formulations of cosmetics, 2nd edition, Verlag Hüthig, Heidelberg, pp. 319-355, to which reference is hereby made.

The cosmetic agents according to the invention may be skin-cosmetic, hair-cosmetic, dermatological, hygienic or pharmaceutical agents. Because of their surface-active properties, the compounds of the formula (I) and the formula (1.1) described above are particularly suitable in compositions for cleansing the skin and / or the hair. Preferably, the compositions according to the invention are in the form of an aqueous solution, a solid formulation (eg a bar of soap or a washing stick)

Foam, emulsion, suspension, lotion, gel, paste or spray. If desired, liposomes or microspheres can also be used.

The cosmetic compositions according to the invention may additionally contain cosmetic and / or dermatological active substances and effect substances as well as auxiliaries. The cosmetic compositions according to the invention preferably contain at least one compound of the formula (I) or of the formula (1.1) as defined above, at least one carrier C as defined above and at least one different constituent, which is preferably selected from among cosmetic active ingredients, Emulsifiers, surfactants, preservatives, perfume oils, additional thickeners, hair polymers, hair and skin conditioners, graft polymers, water-soluble or dispersible silicone-containing polymers, light stabilizers, bleaching agents, gelling agents, conditioners, tinting agents, tanning agents, dyes, pigments, consistency regulators,

Humectants, restockers, collagen, protein hydrolysates, lipids, antioxidants, defoamers, antistatic agents, emollients and plasticizers.

In addition to the compounds of formula (I) and formula (1.1), the cosmetic agents may contain at least one thickening agent. These include z. As polysaccharides and organic layer minerals such as xanthan Gum ^® (Kelzan ^® Fa. Kelco), Rhodopol ^® 23 (Rhone Poulenc) or Veegum ^® (RT Vanderbilt) or Attaclay ^® (Engelhardt). Suitable thickening agents are also organic natural thickeners (agar-agar, carrageenan, tragacanth, gum arabic, alginates, pectins, polyoses, guar flour, locust bean gum, starch, dextrins, gelatin, casein) and inorganic thickeners (polysilicic acids, clay minerals such as montmorillonum). lonite, zeolites, silicas). Other thickeners are polysaccharide gums, for example gum arabic, agar, alginates, carrageenans and their salts, guar, guar gum, tragacanth, gellan, Ramzan, dextran or xanthan and their derivatives, e.g. B. propoxylated guar, and their mixtures. Other polysaccharide thickeners are, for example, starches of various origins and starch derivatives, eg. Example, hydroxyethyl starch, starch phosphate esters or starch acetates or carboxymethyl cellulose or its sodium salt, methyl, ethyl, hydroxyethyl, hydroxypropyl, hydroxypropyl methyl or hydroxyethyl methyl cellulose or cellulose acetate. As thickeners, it is also possible to use phyllosilicates. These include, for example, available under the trade name Laponite ® magnesium or sodium magnesium phyllosilicates from Solvay Alkali and the magnesium silicates from Süd-Chemie.

Suitable cosmetic and / or dermatological agents are, for. As skin and hair pigmentation agents, tanning agents, bleaching agents, keratin-hardening substances, antimicrobial agents, light filter agents, repellents, hyperemic substances, keratolytic and keratoplastic substances, Antischuppenwirkstof- fe, anti-inflammatory drugs, keratinizing substances, antioxidant or as Free-radical scavengers active substances, skin-moisturizing or moisturizing substances, moisturizing agents, deodorizing agents, sebostatic agents, plant extracts, anti-erythematous or anti-allergic active substances and mixtures thereof.

Artificial skin tanning agents that are suitable for tanning the skin without natural or artificial irradiation with UV rays, z. Dihydroxyacetone, alloxan and walnut shell extract. Suitable keratin-hardening substances are generally active ingredients, as used in antiperspirants, such as. Antimicrobial agents are used to destroy microorganisms or to inhibit their growth and thus serve both as a preservative and as a deodorizing substance, which reduces the formation or intensity of body odor. These include z. As usual preservatives known in the art, such as p-hydroxybenzoic acid, imidazolidinyl urea, formaldehyde, sorbic acid, benzoic acid, salicylic acid, etc. Such deodorizing substances are, for. Zinc ricinoleate, triclosan, undecylenic acid alkylolamides, triethyl citrate, chlorhexidine, etc. Suitable light filtering agents are substances that absorb UV rays in the UV-B and / or UV-A range. Suitable UV filters are those mentioned above. Also suitable are p-aminobenzoic acid esters, cinnamic acid esters, benzophenones, camphor derivatives and UV-radiation-stopping pigments, such as titanium dioxide, talc and zinc oxide. Suitable repellents are compounds capable of preventing or repelling certain animals, particularly insects, from humans. This includes z. For example, 2-ethyl-1, 3-hexanediol, N, N-diethyl-m-toluamide, etc. Suitable hyperemic substances which stimulate the circulation of the skin are, for. As essential oils, such as mountain pine, lavender, rosemary, juniper berry, horse chestnut extract, birch leaf extract, hay flower extract, ethyl acetate, camphor, menthol, peppermint oil, rosemary extract, eucalyptus oil, etc. Suitable keratolytic and keratoplastic substances such. For example, salicylic acid, calcium thioglycolate, thioglycolic acid and its salts, sulfur, etc. Suitable antidandruff agents are, for. As sulfur, Schwefelpolyethylenglykolsorbitanmonooleat, Schwefelricinolpolyethoxylat, Zinkpyrithion, Aluminiumpyrithion, etc. Suitable antiphlogistics, which counteract skin irritation, z. Allantoin, bisabolol, dragosantol, chamomile extract, panobenzene, etc.

The cosmetic agents according to the invention may contain as cosmetic active ingredient (as well as optionally as adjuvant) at least one cosmetic or pharmaceutical polymer. These include, in general, anionic, cationic, amphoteric and neutral polymers.

Examples of anionic polymers are copolymers of acrylic acid and acrylamide and their salts; Sodium salts of polyhydroxycarboxylic acids, water-soluble or water-dispersible polyesters, polyurethanes, eg. B. Luviset PUR® Fa. BASF, and polyureas. Particularly suitable polymers are copolymers of t-butyl acrylate, ethyl acrylate, methacrylic acid (for example Luvimer® 100P), copolymers of ethyl acrylate and methacrylic acid (for example Luvimer® MAE), copolymers of N-tert-butylacrylamide, ethyl acrylate , Acrylic acid (Ultrahold® 8, strong), copolymers of vinyl acetate, crotonic acid and optionally further vinyl esters (eg Luviset® brands), maleic anhydride copolymers, if appropriate reacted with alcohol, anionic polysiloxanes, eg. Carboxy-functional, t-butyl acrylate, methacrylic acid (e.g., Luviskol® VBM), copolymers of acrylic acid and methacrylic acid with hydrophobic monomers, e.g. B.

C 4 -C 30 -alkyl esters of (meth) acrylic acid, C 4 -C 30 -alkyl vinyl esters, C 4 -C 30 -alkyl vinyl ethers and hyaluronic acid. An example of an anionic polymer is furthermore the methyl methacrylate / methacrylic acid / acrylic acid / urethane acrylate copolymer available under the name Luviset® Shape (INCI name: Polyacrylate-22). Examples of anionic polymers are furthermore vinyl acetate / crotonic acid copolymers, for example those sold under the names Resyn® (National Starch) and Gafset® (GAF), and vinylpyrrolidone / vinyl acrylate copolymers, available, for example, under the trademark Luviflex® (BASF) , Further suitable polymers are the vinylpyrrolidone / acrylate terpolymer available under the name Luviflex® VBM-35 (BASF) and sodium sulfonate-containing polyamides or sodium sulfonate-containing polyesters. Also suitable are vinylpyrrolidone / ethyl methacrylate methacrylic acid copolymers as are sold by the company Stepan under the names Stepanhold-Extra and - R1 and the Carboset® brands of the company. BF Goodrich. Suitable cationic polymers are, for. As cationic polymers called Polyquaternium INCI, z. B. Copolymers of vinylpyrrolidone / N-vinylimidazolium salts (Luviquat® FC, Luviquat® HM, Luviquat® MS, Luviset Clear®, Luviquat® Supreme®, Luviquat® Care), copolymers of N-vinylpyrrolidone / dimethylaminoethyl methacrylate, quaternized with diethyl sulfate (Luviquat® PQ 11), copolymers of N-vinylcaprolactam / N-vinylpyrrolidone / N-vinylimidazolium salts (Luviquat® Hold); cationic cellulose derivatives (polyquaternium-4 and -10), acrylamidocopolymers (polyquaternium-7) and chitosan. Suitable cationic (quaternized) polymers are also Merquat® (polymer based on dimethyldiallylammonium chloride), Gafquat® (quaternary polymers formed by reaction of polyvinylpyrrolidone with quaternary ammonium compounds), polymer JR (hydroxyethylcellulose with cationic groups) and cationic polymers on vegetable Base, z. As guar polymers, such as the Jaguar® brands of Fa. Rhodia. Very particularly suitable polymers are neutral polymers, such as polyvinylpyrrolidones, copolymers of N-vinylpyrrolidone and vinyl acetate and / or vinyl propionate, polysiloxanes, polyvinylcaprolactam and other copolymers with N-vinylpyrrolidone, polyethyleneimines and their salts, polyvinylamines and their salts, cellulose derivatives, Polyaspartic acid salts and derivatives. These include, for example, Luviflex® Swing (partially saponified copolymer of polyvinyl acetate and polyethylene glycol, BASF).

Suitable polymers are also nonionic, water-soluble or water-dispersible polymers or oligomers, such as polyvinyl caprolactam, z. B. Luviskol® Plus (BASF SE), or polyvinylpyrrolidone and copolymers thereof, in particular with vinyl esters, such as vinyl acetate, z. Luviskol® VA 37, VA 55, VA 64, VA 73 (BASF SE); Polyamides, z. B. based on itaconic acid and aliphatic diamines, as z. B. in DE-A-43 33 238 are described.

Suitable polymers are also amphoteric or zwitterionic polymers, such as those available under the names Amphomer® (National Starch) octylacrylamide / methyl methacrylate / tert-butylaminoethyl methacrylate 2-hydroxypropyl methacrylate copolymers and zwitterionic polymers, as described for example in German patent applications DE 39 29 973, DE 21 50 557, DE 28 17 369 and DE 37 08 451 are disclosed. Acrylamidopropyltrimethylammonium chloride / acrylic acid or methacrylic acid copolymers and their alkali metal and ammonium salts are preferred zwitterionic polymers. Further suitable zwitterionic polymers are methacroylethylbetaine / methacrylate copolymers, which are commercially available under the name Amersette® (AMERCHOL), and copolymers of hydroxyethyl methacrylate, methyl methacrylate, Ν, Ν-dimethylaminoethyl methacrylate and acrylic acid (Jordapon®). Suitable polymers are also nonionic, siloxane-containing, water-soluble or -dispersible polymers, for. As polyether siloxanes, such as Tegopren® (Goldschmidt) or Belsil® (Wacker). In a specific embodiment, the compositions of the invention contain at least one polymer which acts as a thickener.

Suitable polymeric thickeners are, for example, optionally modified polymeric natural substances (carboxymethylcellulose and other cellulose ethers, hydroxyethyl and propylcellulose and the like) as well as synthetic polymeric thickeners (polyacrylic and polymethacrylic compounds, vinyl polymers, polycarboxylic acids, polyethers, polyimines, polyamides). These include the polyacrylic and polymethacrylic compounds, some of which have already been mentioned above, for example the high molecular weight homopolymers of acrylic acid crosslinked with a polyalkylene polyether, in particular an allyl ether of sucrose, pentaerythritol or propylene (INCI name: carbomer). Such polyacrylic acids are u. a. from the company BF Goodrich under the trade name Carbopol ® available, z. Carbopol 940 (molecular weight about 4,000,000), Carbopol 941 (molecular weight about 125,000) or Carbopol 934 (molecular weight about 3,000,000). Furthermore, these include acrylic acid copolymers which are obtainable, for example, from Rohm & Haas under the trade names Aculyn® and Acusol®, eg. The anionic non-associative polymers Aculyn 22, Aculyne 28, Aculyn 33 (crosslinked), Acusol 810, Acusol 823 and Acusol 830 (CAS 25852-37-3). Especially suitable are associative thickeners, e.g. based on modified polyurethanes (HEUR) or hydrophobically modified acrylic or methacrylic acid copolymers (HASE thickener, High Alkali Swellable Emulsion).

According to a preferred embodiment, the agents according to the invention are a skin cleanser. Preferred skin cleansing agents are soaps of liquid to gelatinous consistency, such as transparent soaps, luxury soaps, de-soaps, cream soaps, baby soaps, skin soaps, abrasive soaps and syndets, pasty soaps, greases and washing pastes, liquid detergents, shower and bath preparations such as washing lotions, shower baths and gels , Bubble baths, oil baths and scrub preparations, shaving foams, lotions and creams.

Skin cleansing compositions preferably contain at least compounds of the formula (I) and of the formula (1.1) in a proportion of about 0.001 to 70% by weight, preferably 0.01 to 50% by weight, very particularly preferably 0.1 to 30% by weight. -%, based on the total weight of the product. According to a further preferred embodiment, the agents according to the invention are a shower gel, a shampoo formulation or a bathing preparation. Such formulations contain at least one compound of general formula (I) or (1.1) as base surfactant and optionally at least one amphoteric and / or nonionic surfactant as cosurfactant. Other suitable active ingredients and / or adjuvants are generally selected from lipids, perfume oils, dyes, organic acids, preservatives, antioxidants, thickeners / gelling agents, skin conditioners and humectants.

These formulations preferably contain from 2 to 50% by weight, preferably from 5 to 40% by weight, particularly preferably from 8 to 30% by weight of surfactants, based on the total weight of the formulation.

In addition, all anionic, neutral, amphoteric or cationic surfactants commonly used in personal cleansing preparations may additionally be used in the washing, showering and bathing preparations. Suitable surfactants are the aforementioned.

Furthermore, the shower gel / shampoo formulations additional thickeners, such. Saline, PEG-55, propylene glycol oleate, PEG-120 methyl glucose dioleate and others. Suitable commercially available further thickeners are z. B. Arlypon TT (INCI: PEG / PPG-120/10 trimethylolpropanes Trioleate (and) Laureth-2) and Arlypon F (INCI: Laureth-2). In addition, the shower gel / shampoo formulations may contain preservatives, other active ingredients and adjuvants and water. The compounds of the formula (I) and of the formula (1.1) according to the invention are also advantageously suitable as surfactants for shampoo formulations which may additionally contain other conventional surfactants.

Conventional conditioning agents can be used in the shampoo formulations to achieve certain effects. These include, for example, the abovementioned cationic polymers with the name Polyquaternium according to INCI, in particular copolymers of vinylpyrrolidone / N-vinylimidazolium salts (Luviquat® FC, Luviquat® HM, Luviquat® MS, Luviquat® Care), copolymers of N-vinylpyrrolidone / dimethylaminoethyl methacrylate quaternized with diethyl sulfate (Luviquat® PQ 11), copolymers of N-vinylcaprolactam / N-vinylpyrrolidone / N-vinylimidazolium salts (Luviquat® Hold); cationic cellulose derivatives (Polyquaternium-4 and -10), acrylamide copolymers (Polyquaternium-7). Furthermore, protein hydrolysates can be used, as well as conditioning substances based on silicone compounds, for example polyalkylsiloxanes, polyarylsiloxanes, polyarylalkylsiloxanes, polyethersiloxanes or silicone resins. Further suitable silicone compounds are dimethicone copolyols (CTFA) and amino-functional silicone compounds such as amodimethicones (CTFA). Furthermore, cationic guar derivatives such as guar hydroxypropyltrimonium chloride (INCI) can be used.

According to a further preferred embodiment, the agents according to the invention are cosmetic agents for the care and protection of the skin, nail care preparations or preparations for decorative cosmetics.

In addition, the compounds of formula (I) and formula (1.1) can be used in nasal strips for pore cleansing, in anti-acne agents, repellents, shaving agents, depilatories, personal care products, foot care products and in baby care.

In addition to the compounds of the formula (I) and of the formula (1.1) and suitable carriers, the skin cosmetic preparations may contain further active ingredients and auxiliaries customary in skin cosmetics, as described above. Preferred oil and fat components of the skin cosmetic and dermatological agents are mineral and synthetic oils, such as. As paraffins, silicone oils and aliphatic hydrocarbons having more than 8 carbon atoms, animal and vegetable oils, such as. As sunflower oil, coconut oil, avocado oil, olive oil, lanolin, or waxes, fatty acids, fatty acid esters, such as. B. triglycerides of C6-C3o-fatty acids, wax esters, such as. Jojoba oil, fatty alcohols, vaseline, hydrogenated lanolin and acetylated lanolin, and mixtures thereof.

To set certain properties such. B. improving the feeling of touch, the spreading behavior, the water resistance and / or the binding of active ingredients and adjuvants, such as pigments, the skin-cosmetic and dermatological preparations may additionally contain conditioning substances based on silicone compounds. Suitable silicone compounds are, for example, polyalkylsiloxanes, polyarylsiloxanes, polyarylalkylsiloxanes, polyethersiloxanes or silicone resins. The preparation of cosmetic or dermatological preparations containing at least one compound of the formula (I) or of the formula (1.1) is carried out by customary methods known to the person skilled in the art.

The cosmetic and dermatological agents are preferably in the form of emulsions, in particular as water-in-oil (W / O) or oil-in-water (O / W) emulsions. However, it is also possible to choose other types of formulation, for example drodispersions, gels, oils, oleogels, multiple emulsions, for example in the form of W / O / W or O / W / O emulsions, anhydrous ointments or ointment bases, etc.

Emulsions are prepared by known methods. In addition to at least one compound of the formula (I) or of the formula (1.1), the emulsions generally comprise conventional constituents, such as fatty alcohols, fatty acid esters and especially fatty acid triglycerides, fatty acids, lanolin and derivatives thereof, natural or synthetic oils or waxes and emulsifiers in the presence of Water. The selection of the emulsion type-specific additives and the preparation of suitable emulsions is described, for example, in Schräder, Grundlagen und Rezepturen der Kosmetika,

Hüthig Buch Verlag, Heidelberg, 2nd edition, 1989, third part, to which reference is hereby expressly made.

Preferred fat components which may be included in the fat phase of the emulsions are: hydrocarbon oils such as paraffin oil, purcellin oil, perhydrosqualene and solutions of microcrystalline waxes in these oils; animal or vegetable oils, such as sweet almond oil, avocado oil, calophilum oil, lanolin and derivatives thereof, castor oil, seed oil, olive oil, jojoba oil, karite oil, hoplostethus oil; Mineral oils whose beginning of distillation under atmospheric pressure at about 250 ° C and the distillation end point at 410 ° C, such. Vaseline oil; Esters of saturated or unsaturated fatty acids, such as alkyl myristates, e.g. For example, i-propyl, butyl or cetyl myristate, hexadecyl stearate, ethyl or i-propyl palmitate, octanoic or Decansäuretriglyceride and Cetylricinoleat.

The fat phase may also contain other oil-soluble silicone oils such as dimethylpolysiloxane, methylphenylpolysiloxane and the silicone glycol copolymer, fatty acids and fatty alcohols.

It can also waxes are used, such as. Carnauba wax, candililla wax, beeswax, microcrystalline wax, ozokerite wax and Ca, Mg and Al oleates, myristates, linoleates and stearates.

Furthermore, an emulsion of the invention may be present as O / W emulsion. Such an emulsion usually contains an oil phase, emulsifiers which stabilize the oil phase in the water phase and an aqueous phase, which is usually thickened. Suitable emulsifiers are preferably O / W emulsifiers, such as polyglycerol esters, sorbitan esters or partially esterified glycerides.

According to a further preferred embodiment, the agents according to the invention are a hair treatment agent.

Hair treatment agents according to the invention preferably contain at least one compound of general formula (I) or (1.1) in an amount in the range of about 0.1 to 30 wt .-%, preferably 0.5 to 20 wt .-%, based on the total weight of the composition.

The compounds of the formula (I) and of the formula (1.1) according to the invention are also suitable for styling gels. As gel formers, all gel formers customary in cosmetics can be used. For this purpose, reference is made to the aforementioned conventional thickener.

The compounds of the formula (I) and of the formula (1.1) according to the invention are likewise suitable for the preparation of pharmaceutical compositions.

Suitable pharmaceutical auxiliaries are the adjuvants listed in relevant pharmacopoeias (eg DAB, Ph. Eur., BP, NF) and also other adjuvants whose properties do not conflict with a physiological application. Such substances are for example also in Fiedler, H. P. Lexicon of excipients for pharmacy, cosmetics and related fields, 4th ed., Aulendorf: ECV Editio Kantor Verlag, 1996, described.

Detergents and cleaners

The compounds of the formula (I) and the formula (1.1) according to the invention are also suitable for the preparation of detergents or cleaners, for. For example, for cleaning textile surface fabrics and / or hard surfaces. Such detergents may be in the form of a hand or machine dishwashing detergent, all-purpose cleaner for non-textile surfaces, e.g. As of metal, painted wood or plastic, or detergents for ceramic products, such as porcelain, tiles, tiles are present. The detergents or cleaners according to the invention are preferably in the form of a liquid laundry detergent. If desired, these can also be formulated pasty.

Examples of further formulations in which at least one compound of the general formula (I) or of the formula (1.1) as defined above can be used advantageously are, for example: B. general purpose cleaners, spray cleaners, hand dishwashing detergents for personal, industrial and institutional cleaning;

Humectants;

 Printing roll and printing plate cleaning agents in the printing industry;

Lacquers and color formulations;

Coating agent, for. For paper; adhesives;

 Formulations for spray applications, for example in ink jet inks;

Leather treatment agent;

 Metal treatment agents, such as anti-corrosion formulations;

Cutting, grinding or drilling aids and lubricants;

 Formulations in the textile industry, such as leveling agents or formulations for cleaning yarn;

 Flotation aids and foaming aids. Such formulations usually contain other ingredients such as surfactants, builders, fragrances and dyes, chelating agents, polymers and other ingredients. In general, the compounds of general formula (I) according to the invention can be used in all areas in which a thickening surfactant effect is necessary. Furthermore, the compounds of the general formula (I) are suitable, the solubility of other components, for. B. other surface-active components, such as anionic surfactants to improve. They thus also contribute positively to the formation of clear surfactant-containing solutions.

The invention will be more apparent from the following non-limiting examples.

Examples

Example 1 :

In a continuous falling film reactor with jacket cooling and SO3 gassing, 600 g of a technical grade laurylolactolate (68% monoester) were reacted with sulfur trioxide at 40.degree. The molar ratio was 1.2 mol of SO3 per mole of lauryloligolactate. The sulfur trioxide was expelled by heating from an appropriate amount of 65% by weight oleum, diluted with nitrogen to a concentration of 5% by volume, and contacted via a nozzle with the lauryl lactate film. Then it was stirred together with 50 wt .-% sodium hydroxide solution in a 1 wt .-% solution of potassium dihydrogen phosphate and neutralized at a pH of 5.5 to 7.5.

analytics:

 Anionic surfactant content 14.5% (MW = 374.4 g / mol)

Unsulfonated: 2.47%

 Water according to Karl Fischer 83.9%

Na ₂ S0 ₄ : 1, 7% Comparative Example:

In a continuous falling film reactor with jacket cooling and SO3 gassing, 600 g of a lauryl lactate (87% monoester) were reacted with sulfur trioxide at 40.degree. The molar ratio was 1.2 mol SO3 per mole of lauryl lactate. The sulfur trioxide was expelled by heating from an appropriate amount of 65% by weight oleum, diluted with nitrogen to a concentration of 5% by volume, and contacted via a nozzle with the lauryl lactate film. Then it was stirred together with 50 wt .-% sodium hydroxide solution in a 1 wt .-% solution of potassium dihydrogen phosphate and neutralized at a pH of 5.5 to 7.5.

analytics

 Anionic surfactant content: 15.4% (MW = 368.5 g / mol)

 Unsulfonated: 1, 3%

 Water according to Karl Fischer: 82.8%

Na ₂ S0 ₄ : 1, 72%

Application Test:

The substance from Example 1 and the comparison substance were adjusted to a concentration of 12% and increasing amounts of NaCl were added. The viscosity of the solutions was determined using a viscometer: Brookfield Dil + pro at a measuring temperature of 22 ° C.

The example of the invention shows a higher viscosity increase at lower NaCl contents. Furthermore, the foaming behavior of the two substances was tested with a Sita rotor foam measuring device (1, 0 g / l, 30 ° C, 1300 rpm, pH = 5.5). Example 1 Comparative Example

 Stirring time foam volume

 [s] [ml]

 0 0 0

 10,231,237

 20,392,400

 30,532,539

 40 765 765

 50 829 828

 60 851 849

 70 860 857

 80 866 861

The foaming behavior of both substances is identical within the scope of the measuring accuracy.

Claims

claims 1 . Compounds of the general formula (I)

in which hydrogen or a linear or branched aliphatic hydrocarbon radical having 1 to 30 carbon atoms and 0, 1, 2 or 3 double bonds, the radicals R ^{2 are} independently selected from hydrogen, methyl, ethyl, -OA, -COOR ⁴ , -CH ₂ -OA and -CH ₂ -COOR ⁴ , wherein the radicals R ^{4 are} hydrogen or a linear or branched aliphatic hydrocarbon radical having 1 to 30 carbon atoms and 0, 1, 2 or 3 double bonds, the radicals R ^{3 are} independently selected under hydrogen, methyl, ethyl, -OA, -COOR ⁵ , -CH ₂ -OA and -CH ₂ -COOR ⁵ , wherein the radicals R ^{5 is} hydrogen or a linear or branched aliphatic hydrocarbon radical having 1 to 30 carbon atoms and 0, 1 , 2 or 3 double bonds, A is H or -SO3B, wherein B is hydrogen or a cation equivalent, n is an average of at least 0.1, m1 and m2 are independently 0 or 1, provided that at least one of the radicals A stands for -SO3B, and with the proviso that at least one of R ¹ , R ⁴ or R ^{5 is} a linear or branched aliphatic hydrocarbon radical having 1 to 30 carbon atoms and 0, 1, 2 or 3 double bonds. 2. Compounds (I) according to claim 1, wherein m1 and m2 have the same meaning. Compounds (I) according to any one of the preceding claims derived from lactic acid, glycolic acid, malic acid, tartaric acid or mixtures thereof. Compounds (I) according to any one of the preceding claims, which are selected from compounds of the formula (1.1) o o R- ^■ O- ^■ C CH (CH ₃ ) O- ■ C CH (CH ₃ ) -OSO ₃ B (1.1)  in which is hydrogen or a linear or branched hydrocarbon radical having 6 to 30 carbon atoms and 0, 1, 2 or 3 double bonds, B is hydrogen or a cation equivalent, and n stands on the average for a value of at least 0.1. Compounds (I) according to any one of the preceding claims, wherein n is from 0.1 to 100, preferably from 0.15 to 50, especially from 0.2 to 20. 6. Compounds (I) according to any one of the preceding claims, wherein at least one of R ¹ , R ⁴ and R ^{5 is} methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-. Butyl, n-pentyl, isoamyl, n-hexyl, 2-ethylhexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, 2-propylheptyl, n-undecyl, n-dodecyl, n-tridecyl, n- Tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, arachynyl, behenyl, lignocerinyl, melissinyl, isotridecyl, isostearyl, oleyl, linoleyl, Linolenyl or a combination of at least two of these radicals. 7. Compounds (I) according to any one of the preceding claims, wherein at least one of the radicals R ¹ , R ⁴ and R ^{5 derived} from linear saturated alcohols having 8 to 18 carbon atoms. 8. Compounds (I) according to any one of the preceding claims, wherein at least one of the radicals R ¹ , R ⁴ and R ⁵ of a mixture of linear saturated  Derived Ci2- / Ci4-alcohols. 9. A process for the preparation of compounds of the general formula (I), in which a) at least one hydroxycarboxylic acid of the general formula (I.A) HOC (CHR ² ) _m1 CHR ³ - OH (LA) wherein R ² , R ³ and m1 are as defined in any one of claims 1 to 8, in an esterification reaction, wherein the esterification is carried out in the presence of at least one alcohol R ¹ -OH, wherein R ¹ as in one of claims 1 is defined to 8 or the product of the esterification of the hydroxycarboxylic acid (s) (IA) is subsequently reacted with at least one alcohol R ¹ -OH, the reaction product from step a) is reacted with a sulfating agent, and c) optionally the reaction product from step b) at least partially neutralized with a base. 10. The method of claim 9, wherein the sulfating agent used in step b) comprises SO3 or consists of SO3. 1 1. Cosmetic or pharmaceutical composition comprising a) at least one compound of the general formula (I) as defined in any one of claims 1 to 8, b) at least one cosmetic or pharmaceutical active substance, and c) optionally at least one of the components a) and b) different cosmetic or pharmaceutical excipient. Cosmetic composition according to claim 1 in the form of hair shampoos, shower gels, soaps, syndets, washing pastes, washing lotions, scrub preparations, bubble baths, oil baths, shower baths, shaving foams, shaving lotions and shaving creams. Detergents or cleaning compositions containing at least one compound of general formula (I) as defined in any one of claims 1 to 8. Use of at least one compound of the general formula (I) as defined in any one of claims 1 to 8 as surface-active substances. 15. Use of at least one compound of general formula (I) as defined in any one of claims 1 to 8, as anionic surfactant for cosmetic agents, pharmaceutical agents, detergents and cleaners.